Thoreau may have said that “Wealth is the ability to fully experience life”, but what he should have added is that it is also the ability to fully experience the crazy. From mind-blowing bridezillas to caviar-eating kids, these shocking Reddit stories reveal how the ultra rich really are different from the rest of us. And not in a good way.
1. New Bed, Who Dis?
I'm a wedding planner and had honeymoon clients with a unique request: they refused to sleep on any mattress others had used before. So, we had to get them a brand-new mattress at each hotel they stopped at. These fancy mattresses weren't cheap -- over $5000 each! And they visited five hotels in all.
The kicker is, they only used each mattress for a couple of nights tops. And, guess who had to deal with the removal and disposal of these barely slept-on, pricey mattresses? You guessed it, me.
2. Best Seat In The House
I'm an art student but also a gardener in a super-rich area. When I chat with my clients about my school stuff, some get all excited and want to show off their art stash. Once, I was in someone's bathroom, still in my messy gardening gear, and they were all proud of their real deal Picasso hanging above their toilet.
3. Hogwarts And All
A coworker's daughter had her wedding booked at a local spot. A couple of months before the big day, though, that venue showed up in a Harry Potter movie, and things got nuts. A month out from the wedding, the venue called her up.
Crazy enough, they asked if she could push back her wedding a month. Of course, she said no. All the invites were out, family was traveling from all over the globe, and flights and rooms were booked. Changing all of it would be a real headache.
Even so, she eventually did shift her wedding. When she found out why they asked her, her mind was blown. Seems this mega-rich family with a kid obsessed with Harry Potter wanted the venue for a birthday bash the same weekend.
The bride-to-be only agreed to move dates after the loaded dude agreed to foot the bill not just for the wedding, rebooking travel and rooms, the flowers, and the photos, but even her new house's mortgage! It added up to a few hundred grand, but to them, it was like pocket change.
4. Literal Helicopter Parents
I was at a summer camp with a bunch of rich kids. On the parents' demand, the camp made a chopper pad nearby. This meant parents didn’t have to drive for hours just to pick their kids up. Plus, a lot of these parents gave massive tips to counselors who took care of their kids for the summer.
I didn’t get tipped since my kids were on scholarship, but some of my coworkers got tons – we're talking hundreds of bucks, a Macbook Air, or even plane tickets for visits to the families, no matter where in the world they were. One was, like, a trip all the way from Australia to LA. As a TIP!
5. A Fine Mess
During my divorce, finding a parking spot at the courthouse was a nightmare. It wasn't just crazy pricey, but also had a two-hour cap. I thought surely my attorney had some parking perk. But, his response blew my mind. According to him, the parking madness is just a money-making scheme for the city, but he'd found a sort of workaround.
Turns out, attorneys get the short end of the parking stick too. So, his firm chose to absorb the daily parking fine hit rather than having the attorneys stress about relocating their wheels every two hours. When the city first introduced this two-hour parking rule, they tried to stick to it. But court is a wildcard; times fluctuate and the judge wouldn't care less about your parking woes.
So now, their law firm shells out thousands monthly in parking fines, lining the city's pockets.
6. All You Have To Do Is Ask
My friend's dad joined this swanky country club because his kid was on their tennis team. Randomly one Wednesday, he got to play poker with the other members. When they decided to grab some drinks, the waiter handed them a wine list. Then this old dude was like, "No, give us the PROPER list."
Turns out, there was this super posh list only on special demand. Ever since I heard this story, I've been curious about all the exclusive perks these well-informed folks have up their sleeves.
7. A Very Particular Set Of Skills
I interviewed for a nanny job in a downtown high-rise. The deal was for a divorced guy with two kids who needed me to stay over four nights a week. Although I'd be missing my cats and my routine, my recruiter was keen so I went for it. After that, this guy's "executive assistant" chatted with me, this very proper lady in her 60s. She was close with her boss, the children's father—maybe too close in an odd kind of way.
But one of the questions gave me pause. It asked how annoyed I'd be if I had been told to pack for a trip to Florida, but then had to change to a trip to Aspen at the last minute instead. Apparently, these folks owned a private jet. I also got to hear about how the dad struggled to look after his sick kids one night—a story that the exec assistant was oddly warmed by.
In between, she emphasized how this dad needed a nanny 24/7, hence all the nights I'd need to stay over. Post interview, while on our way to the elevator, things got awkward. She made a snide comment about wearing jeans to an interview. My reasoning: Snowstorm outside plus jeans are good for a play-date-turned-interview. Also, this ain't an office gig, it's a nanny role.
After me, they interviewed loads of people from all over the city. One lucky girl got to meet the big man for a lunch date—and much more. But in the end, they took a U-turn and decided to stick with their old nanny for another year. I was secretly relieved!
8. More Dollars Than Sense
There's this bar I used to hit up with a game: coin toss for your drink. You ordered, tossed a quarter - heads, you only paid a quarter; tails, you paid full price. Met these dudes there who loved ordering expensive bottles just for the kick of flipping the coin.
When they'd lose, they'd drum their feet and cough up the cash. But whoever got heads, they'd all go bonkers, paid the quarter, and tipped the bartender the cost of the bottle. We're talking bottles in the hundreds here. And they'd do this all night, just for the rush of flipping a coin. The bar staff absolutely adored them.
9. A Deck Too Far
There was this loaded kid at my college who had a fresh ride each semester. During his last term, he protested a $30 parking ticket he got for parking in a faculty-only spot. He said he only parked there because he "didn't feel like" parking in the far-off lot and walking for 10 mins.
His argument? "I always park in those spots knowing I have to pay the fine. This time wasn’t even a faculty spot." So, the admin checked his record and boom! Turns out in the last four years, he'd bagged over 300 tickets for parking where he shouldn’t.
Surprisingly, he’d paid every single one promptly. His motto was pretty much, “Who cares? I hate walking. I'll just park in a prof's spot and cough up the fine." Oddly enough, his lone disputed fine got dropped, and honestly, he was probably right about it not even being a faculty spot.
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10. Queen Of The Machine
When I visited Vegas, I hit up a casino with a VIP zone. It had a view of the slot machines that cost $100 a pop. While there, I noticed this average older woman playing one of these machines like my grandma would play penny slots. Within minutes, she'd spent enough cash to get my truck, and it didn't even seem to faze her.
11. Calling All Cars
I was over at some rich dude's place to fix not just one, but two of his generators. I rang him up on the call box and he let me in. As I drove up the rocky driveway, I passed his garage and my jaw dropped. This wasn't just a garage, it doubled as a basketball and tennis court. It was practically a mini-parking lot.
Inside, the guy had a whopping 13 cars, from basics like a Chevy Suburban, Mini Cooper, and Subaru Outback to a couple of high-ends like Bentleys and a Rolls Royce, oh, and a stretch Lincoln limo. The guy walked me through four separate rooms just to reach the generators. Afterward, we headed back up to where my truck was parked.
The guy, chillin' in his sandals and a Rolling Stones tee, casually points and says, “Oh, by the way, if you gotta go, the bathroom's right behind the Bentley”. I couldn't believe how laid-back the dude was about it.
12. He Broke The Bank
My old boss saw some additional fees on his bank statement that he thought were too much. He phoned the bank, and nobody could explain the charges, nor did they offer to drop any.
So, as payback, he decided to close all his bank accounts. This meant he made a cash payment for the remainder of his multi-million dollar mortgage. When he told me that, my jaw dropped. I was amazed that he had that sort of cash in his checking account to clear his mortgage. But his choice was to get a mortgage instead of paying for his house with cash.
When the bank's mortgage team recognized what he'd done, they begged him to return and refinance because of the substantial interest loss. But his response? A hard no.
13. Who Pays The Bills Around Here?
My boss mixed up the mail and got our neighbor's Bloomingdale's bill. He didn't check the name on it, thinking it was his wife's bill. That one mistake cost him HUGE. He was forking out cash for YEARS for the next-door neighbor's Bloomingdale's stuff without catching on.
The neighbor's reaction? Totally stunned. My boss? He's super loaded, and so he coolly just told the neighbor it was his Christmas gift.
14. A True Baller
You remember Paul Allen, the guy who co-founded Microsoft? Well, he used to have this huge 414-foot yacht. There was a freaking basketball court on one of its decks. And here's the insane bit - sometimes while playing, the basketball would go over the side, into the sea. But, instead of losing that ball forever, Paul came up with an idea. He got a guy on a smaller boat to follow his yacht around, just picking up all the stray basketballs.
15. Very Petty Cash
This guy I know bought a whole building to kick out a tenant. Yup, you guessed it, his cash was all from the family, and literally no one could stand him. He was born with a silver spoon, thinking he was the king of the world. I never really got to know the poor bloke who got kicked out, but word is, he didn't "respect" Silver Spoon enough — so he got a tough lesson.
16. One Rich Son Of A Beach
I had a job at a top-notch Maldives resort, catering to the rich and famous. Some might show up in a private plane—there was even this one family who always had their mega-yacht ready for their once-a-year visit. But still: I guarantee you won't believe the craziest story I've got from there.
This one time, I was assigned to Mr. Sergei Popov, who's a big shot rich guy living in Switzerland. You see, he wasn't traveling with his wife, but another woman. They flew into Maldives’ capital, Malé, on a private jet. From there, you've got various options to reach our resort...
Whether by boat in 45 minutes for your regular Joe, or a cozy 40-minute yacht ride for those a bit wealthier, or a straight 12-minute seaplane ride for the total ballers. Guess which one Popov picked? Yup, the seaplane.
Just a quick side note, I aced this job thanks to my language skills—I can speak Russian, English, Thai, and Mandarin. So, I'm waiting for them at the seaplane dock for the usual meet and greet.
They step out of the plane, I do my greeting in Russian, they respond in English. Great, keeping up that high-society vibe. We hop on a golf cart and I take them around the island, then to their villa. It's not the topmost fancy villa, but they want fancier. I get them to the only vacant presidential villa. It finally matches their standards.
We agree on $12,000 extra a night for that. So now, their nightly rate is a whopping $27,000. This luxury villa is crazy huge, and they get a private phone to call me anytime. Then comes the outrageous requests. His girlfriend has a birthday coming up and I'm to arrange a surprise. Budget? No worries.
Consider it done. A reserved seat at the bar every evening? We don't usually do that, but for you, done. His niece is coming over next day and, yep, I need to get her settled in another detached villa. The moment I see her, I know something's up. She arrives in this mink coat despite the crazy heat, with nothing but a small purse.
Sure doesn't look like a "niece". Anyway, she dashes for the boutique, wants to get some tropical clothes and fill up her empty villa. She's 18. Yay? Next day, housekeeping calls me urgently. The villa is trashed. Thank God for the scorching Maldives sun, took my mind off it.
Now, "niece" is leaving. Then it's the girlfriend's birthday. I've got a secluded pavilion by the sea, loaded with rose petals from Sri Lanka, and hundreds of floating candles. Classical music, expensive wine, and exclusive staff, all set.
I check on them after dinner, he's pretty thrilled and appreciates everyone's efforts. We did appreciate the $14,000 he spent on that dinner too. Everyone's happy. Next day, they act like we're pals. He gives me his departure plan and a $2,000 tip.
Overall, their stay cost $230,000. Welcome to my job!
17. Score!
My friend snagged a brand new, six-burner stainless steel oven for cheap on Facebook Marketplace. It sounds like some well-off folks bought a vacation home in a nearby resort town but dumped the appliances because they didn't match their decor.
They were never even used because the house had just been refurbished before they bought it.
18. Them’s The Breaks
This dude bumped me in traffic, smacking into the right side of my ride. I was ready to go ballistic, grab his insurance details. But when I jumped out, he floored me. The moment he saw me, buddy just passed me a check for $6,500, no questions asked. The repairs were just $200?
19. Free Gift With Purchase
I used to work at a high-end jewelry shop. One day this cranky woman and her husband walk in, totally ignoring me. But I didn't let that stop me. I followed them around, trying to chat. She started asking about stuff in the display case and bought everything I mentioned without even looking at the prices or making a fuss.
She dropped over $33,000 in less than 10 minutes. But then, while I'm gift wrapping it all, she and her husband spent that time demanding free stuff. They threatened they wouldn't shop here again unless we gave 'em the priciest freebies we could find. Our team ended up giving her a load of freebies—even though $33 grand isn't really that much when you're talking luxury retail.
Turns out, every time she's visited in the past, she's been a big spender. So I guess it all adds up.
20. Breaker High Meets Contagion
When the lockdown started, my buddy, a teacher in a DC private school, got approached by some parents. They asked her if she could tutor their kids on their Caribbean cruise, while everyone was avoiding the virus. They wanted her to live and teach on their yacht, five days a week.
She didn't do it, though. But man, that was one of the most extravagant ways I've seen someone spend dough.
21. Mazel Tov!
Back in high school (around 2005), I got invited to the craziest bat mitzvah ever. This wasn't your average 13-year-old's party, they spent $3.5 million on the bash. It had a real circus tent that could fit over 500 people, a magic show with full-grown elephants and tigers.
These beasts were shipped all the way from Las Vegas to Westchester, New York. Add to that, there was a top-notch arcade tent, making Dave and Buster's look lame in comparison, and full valet parking plus limo services from your car to this massive estate's main entrance. Each guest got a goody bag filled with swanky stuff, including an iPod mini, which btw was how I got my first iPod.
22. It’s Been A Slice!
I work at a posh pizza joint and thought I had witnessed pretty much everything: customers splurging big bucks on a single order, folks journeying from different towns and wanting their pizza hot and ready on arrival, and so forth. There was this one time where a dude purchased a dozen pizzas and sampled a tiny piece from each one. Following that, he chucked the remainder in our trash.
Initially, we thought he must be taking it in bulk for a party or office shindig. Turns out, his sole purpose was to taste every possible topping mix. On the brighter side, he did leave us a $100 tip, which makes up for a lot.
23. Someone In Cambodia Loves Me
My rich friend got kidnapped up on his holiday in Cambodia, where he'd been partying and clubbing for months. It was no surprise someone decided to grab him and so, he was stuck sobering up in a grimy shack while the kidnappers demanded cash for his freedom. But they had no clue what they were in for.
Good for him, his trust manager had solid connections. A phone call or two later, a high-ranking local showed up with a huge security team, and just like that, the kidnappers let him walk.
24. It’s A Small World After All
A student at my friend's university, who's from overseas, booked a flight from Spain to Canada. They were hitting a music fest with some buddies. She snagged her ticket on a Thursday, the event was the very next day, and she'd be home by Sunday. She definitely went all out on a first-class ticket.
"No biggie, just zipping across the Atlantic to hang with my friends this weekend."
25. Spoiled Rotten?
I used to work at this swanky hotel, and this fella checked in with his little girl, about 6 or 7, and her older cousin, maybe babysitter, around 14. This guy was out all day being a tourist and left the two girls in the room on their own. Oh, did I mention they were rolling in dough?
The little one had a fondness for ice cream and was always ordering a scoop, tipping the server $50 each time. Then she'd ring again after 10 minutes for more, slapping down another $50 tip. This went on for a while, so we took turns with the room service and everyone got a bit of the action. But it got to a point where it was awkwardly too much.
26. Kids These Days
Since I moved to this fancy town, it's crazy to see so many little kids ordering $300 caviar for dinner at the restaurant I work at. One family that does this is my favorite, though—they always leave a $1000 tip.
27. Smashed Out Of Their Minds
During my bartending days, there was this smug guy, probably in his 30s, who wanted to buy all the champagne we had for him and his four friends. I didn't agree to it, but offered two bottles and told them they could order more later. He agreed and that's when I took my break to have a smoke. Little did I know what he had planned.
Then, I noticed the same guy and his friends after 10 minutes, running out the door with as many champagne bottles as they could carry. But that wasn't all. They went on to smash the full bottles into the street while laughing and howling. Apparently, my fellow bartender had allowed them to buy all our champagne, hoping for a generous tip.
So, these guys just went wild, breaking bottles in the street and even going back for more. We managed to stop them and called in the cops, but they fled before anyone could arrive. The tab was astronomical. Three paid $2,200 with credit card, and one gave about a $5,000 cash.
28. Not-So-Fair Play
I used to wait tables at a sports bar, and this place screened all major pay-per-view events. One busy night, this dude at my table whips out a $100 bill and asks if I could change it into 100 one-dollar bills. I told him it'd take some time since I'd have to get my manager to open the safe. But he was okay waiting.
I finally got him the 100 singles and the game continued. The final, likely title-deciding match had just ended, and the winner was announced. That's when this guy did the weirdest thing - he tossed all his dollar bills into the air and yelled out, "There's your tip!" Talk about a bizarre way to mess around with your server, right? And such a long-drawn stunt too.
29. Bling The House Down
There's this local politician who also runs a shopping chain. His son, who's about three years older than me, is always decked out in gold chains and diamonds. I once spotted him at a cafe with his buddies, flaunting his wealth as usual.
The moment that really got to me was when the waiter brought their bill. This guy hands over one of his less flashy rings as payment, then waves the waiter off like he's a pest. The disrespect was enough to make me feel queasy.
30. Miami Vice
A college dorm mate of mine vanished for nearly a week once. His explanation was bonkers when he got back - he said he got held up by the FBI! It seems he knew this loaded kid who flew them all out to Miami for a bash at the Four Seasons suite.
Here's the crazy part - this wealthy guy, even with an allowance of $40K a month, was sneakily lifting from his dad's business to cover his extra expenses because, believe it or not, $40K wasn't enough for him! The Feds traced this guy to the Four Seasons and crashed the party.
31. One Person’s Trash…
I once lived close to Wesleyan University - you know, the school from "How I Met Your Mother." Each year, when the wealthy students went back home, we'd set off on a dumpster diving mission. You won't believe it, but these guys would chuck away perfectly fine laptops, iPods and more. Talk about being so loaded that a $500 gadget seems disposable.
32. Bone Appetit!
I'm chilling at this swanky eatery in Mexico City, when this dude strolls in with a couple of dogs, and gives the waiter a slight nod. The waiter gets it and returns with a drink for the guy and a pair of giant raw steaks. The dude sips his drink, contentedly watching his dogs chow down on these $50 slabs of raw meat.
Then, like a boss, he just up and leaves into the night. Talk about making a statement!
33. A Friend With Benefits
My one friend? She is absolutely swimming in cash, along with her entire family. Super cool people, big-hearted. But they're kinda clueless about the average joe's financial struggles. Take the mom, who totally overhauls their house decor a couple of times each year.
She doesn't just switch up some cushions. Nah, it's the full works - new furniture, paint, floors, trinkets, the lot. She especially loves decking everything out for holidays. So much that she buys brand new decorations every time. My friend is like Santa, giving away her mom's passed-down Christmas stuff.
They've got a mini-zoo at home - dogs, cats, fish, exotic birds, even horses. But the family doesn't look after them, they've got a whole staff for that. There's a dude who handles the swanky fish tanks a few times weekly and another person taking care of the bird room daily.
Don't even get me started on the separate caretaker for the dogs and cats, plus the horse crew. None of the fam even rides the horses!
Their lavish lifestyle extends to food too. You'll find caterers dropping off meals at the house randomly. I'm talking a feast so huge that my friend is calling up buddies to help polish it off.
Just last week, I was invited for dinner. Why? They catered a prime rib dinner spread for 20 folks. And it wasn't even a special occasion. Just a plain old Wednesday. Madness.
34. The Most Magical Place On Earth
I'm an accountant. One of my worst experiences was with this businessman, who got the wild idea to take his whole family, like 20 people, to Disney World, and tried to count the whole trip as a business expense!.Of course, we caught him out and told him that's seriously not cool. If he got the boot, we'd get it just as bad, maybe even losing our licenses.
But he wasn't having any of it! We ended up having end our relationship with him, which I think is the only time we've ever had to do that to a client.
35. Many Unhappy Returns
My friend, a woman over 50, got a cool birthday deal from her loaded folks - they gave her a grand to spend on a gift. She decided to splurge on QVC, buying and returning a ton of clothes, footwear, and gadgets. Most of it was useless stuff, to be honest.
So, my friend was playing this buy-return-buy game, probably assuming she'd hit her one grand mark. But, after a month, the reality was a whopping $11,000 in bills. It was such a mess that she and QVC couldn't agree on what she got, sent back, or had to pay. And the fallout was downright hilarious!
QVC ended up banning her from shopping with them. Like, forever! No surprise, her parents were pretty miffed and had to clean up the chaos. They figured it out with QVC and agreed on a number somewhere between $5,000 and $11,000. But QVC made it clear—no more orders for ever again, not even if hell froze over.
36. Sometimes You Eat The Bar…
I was grabbing a bite with my future boss to chat about a job offer he'd given me. I believe he was trying to win me over. We met at a tapas joint and I was grappling with the big menu, trying to figure out the right amount to order, when he suggests, “Let's just get everything". I was floored. Sadly, I had to bounce back to my home country, so I missed out on this chance. Honestly, working with a guy like that could've turned my life around, but well, that's life.
37. Read The Room
At uni, we all had cheap junkers, except for one rich guy who drove super expensive cars. One day, he started telling us off about bad tires and not fixing a broken window. He then tried to tell us all about how we should fix our cars because to him, a thousand bucks apparently ain't much. Dude had crashed his fancy car and easily got it repaired. But dude, we don't all have a stash of spare parts lying around!
38. Champagne In The Butt
I had a gig at a club over in Ibiza. The deal was, when you buy five bottles of bubbly, these gorgeous girls rock up, bikini-clad, sparklers in hand. Total show-stopper. People would go all out, buying boatloads of champagne just to flex on the other wealthy folks. Heck, some nights we ran out of space for all the bottles!
Funny thing is, they rarely even drank the stuff.
39. Just Plane Evil
There's this rich dude who spruced up the insides of his two planes, including freshening up the leather seats. He started freaking out because he noticed that the stitching on some of the seats looked different. He figured it was because two different people worked on the seats at Cessna, which really ticked him off.
So what does he do? Sends the planes back to Cessna AGAIN to get the seats all redone by the same person.
And get this: this same guy also whined about how the Affordable Care Act was gonna stop his company from shoving employees off their health insurance once they hit a lifetime limit. Oh yeah.
And the kicker? The dough this guy's company saved by booting sick employees off their insurance was just about the same as the cost to pimp out his planes – almost a million bucks. Figures, right?
40. Sick Burn
My film class teacher, who used to be a director, loved sharing his old stories. We'd often spend time after class just soaking up his stories. Back when he was a student himself, he had a friend who ended up being a super successful executive. They made a point of catching up once or twice a year, having dinner and just chilling.
His exec buddy always picked the fanciest places and stubbornly footed the bill, despite my teacher's protests. Once, after a particularly great year, my teacher was adamant that it was his turn to pay. His friend agreed, and they went for it, only to see the bill roll in at $12,000. My teacher, though taken aback, was ready to swallow his pride and reluctantly pay.
Yeah, he was a notable director, but the work wasn't always there. Just when he was about to shell out, his friend chuckled, swiped the bill away saying he's got it covered. My teacher quipped that he would've needed a whole year's salary just to live a day like his friend. Talk about extreme!
41. Insufficient Memory
I once had this job at the smoothie bar at an Equinox gym. One of our regulars was this guy with a really odd issue. He'd always be complaining how he was so tied up with things that he kept forgetting to pack his gym bag when coming to the gym. So, what did he do? He'd simply hit up our retail section every time and splurge on a complete set of workout gear, including shoes.
Now, just to give you an idea, an entire set like that cost like my rent for a whole month! I used to chat with the crew in the retail section every once in a while, and they told me that surprisingly, this guy never brought back any items for a return.
42. Money Can’t Buy Poverty
I'm a teacher at a fancy international school with some mega-rich students. In a pre-calc lesson, we talked about something always useful: How exponential functions apply to compound interest. I gave my mini lecture and one super-rich girl wasn't having it.
She's like, "When will I need this?" I tried to explain why once again and she shots back, "Why would I ever borrow money?" I had to keep my cool and I gave my explanation another shot, using a bigger example this time. I asked if she'd prefer $50 now or $100 in a week.
"I'll take the money now," She rolled her eyes, "Why wait a week for an extra $50?" Oddly, she ended up with a UN internship fighting poverty and she was also the one poking fun at the scholarship kid for being poor. I swear I'm not making this up.
43. Insanely Practical
My friend lived in the city center and snagged an internship out in the burbs. She needed a car but had zero experience buying one. No worries though, her loaded dad sent money to bankroll her ride. After sorting some bank stuff, she ended up stuffing a bag with thirty grand and hit the subway.
She rolled up to the Honda dealership. She's not a snob, just kinda clueless about cars. She dropped the cash right then and there for the car. And just like that, she scored a new ride—and a boyfriend from the dealership.
44. You Had Me At $800 Eyelashes
One client threw a super expensive wedding — think top-notch city venue, designer everything, basically a money extravaganza. The amount they splurged was ridiculous. But anyway, all that cash didn't prevent drama on the wedding day.
Here's what happened. The bride lost it big time when her mom rocked up wearing the 'wrong' shade of green. Like, legit spent over an hour yelling and crying, totally messing up her pricy makeup and causing everything to be delayed by a whole day. Heard she had to fork out more than the initial venue rent because of this and all the vendors charged overtime 'coz we had to stay past midnight.
The funniest part? The bride didn't even work. Her folks footed the entire bill. And the cherry on top: The marriage tanked after less than half a year.
45. What A Weirdough
So, my dad is a carpenter. This one client of his had a wacky idea of getting a huge, operational pizza oven built in their home kitchen. And, well, he did it. After my dad finished up and collected his paycheque, he had to ask them – did they make a lot of homemade pizzas with this mega oven or what? The answer was ridiculously funny. The client said, "Nah, we rarely make our own stuff. My wife just needed a decent place to keep Domino's pizzas warm".
46. Gaming The System
I was chatting with this kid and we started talking about video games. He mentioned that his PS4 had kicked the bucket. When I asked what happened, he shrugged, said it just stopped working one day when he tried to game on it. He didn't seem too fazed, and I was about to find out why. Kid pulls out a fat wad of $700 from his jeans, says his dad gave it to him as a replacement fund.
I suggested maybe fixing it first, but he shook his head, said he'd just get a new one like he always does. I mean, it's not like it's his fault he's used to just buying whatever he wants, but getting a brand-new console on the same day it broke is definitely not something my folks would approve. They'd more likely say, "Try a $40 repair check first", before they even consider splashing on a fresh one.
47. Not A Light-Bulb Moment
I'm employed by an electric company that charges a bit more than $200 an hour. We're a union-affiliated, commercial, and industrial-approved operation with experienced workers. What surprises me is the huge number of clients who don't mind paying this much just to get their light bulbs replaced. Some folks just can't manage everyday tasks.
48. That’s Mr. Cheapskate To You
I used to work for this really rich guy - but not the type you're thinking of. Every week, we'd grab lunch at our local Subway. He'd pile up on free salt, pepper, napkins, you name it. It almost seemed like he enjoyed scamming the place... getting freebies, saving his dough.
Once, he invited me to see a college football game. I was to meet him at his place which had a garage crammed with seven top-end cars. But weirdly enough, he wanted me to drive us in my old '02 Jetta, the one with the busted windshield. And he didn't let up complaining about my car throughout the ride. After arriving, I ended up buying snacks for him and his kids. And the cherry on top? The seats weren't even that good.
49. The Upper Crust
I went to private school with a group of really wealthy kids. I've got heaps of tales to tell but the best one is about my friend's sister. This girl had a thing for a particular type of bread and she wanted it for her weekend breakfast. And it absolutely had to be fresh. So, each weekend, their househelp would have to fly—to ITALY—in their family's personal jet just to bring her back some fresh bread.
50. Super Rich And Rather Strange
I'm a concierge at a fancy resort, and this one night, my boss calls me when I'm chilling at the bar. He says there's a super-VIP guest coming—some friend of the big boss. Didn't even have time to google the dude. Tossed back a few more shots, got back into my work gear, and headed for the pier to meet the guy.
The dude turned up after midnight, and he was all eccentric energy, like someone from a crazy novel. He decides my name is Dimitry and starts listing the things he needs. The guy needs expensive champagne, snacks, floodlights to show off his villa, and his shirts color-coordinated in the closet. And then he wants the joint cleaned, so I roll up with the cleaners and this guy blew my mind.
In the bathroom, he used up every single toiletry and threw out two full rolls of dental floss. Freaky. He sends me to meet his friends and sort out their spa bookings. His friends turn out to be three stunning babes and a dude who looks like a mix of all the handsome actors, and apparently, he's some famous director's son. So I take them to the bar, and soon the VIP dude calls me to bring them back to his lit-up, champagne-filled villa.
The guy starts bragging about his private jet, teasing the girls about flying to Paris Fashion Week. Partying ends around 4 am, and I crash, only to be woken up by Mr. VIP's breakfast order at 8 am. He orders up a feast, and I gather it's all just for him. This guy then ropes me into listening to a business call, and he's going off on some lady because the numbers are wrong. Post-call, his friends show up for their massages.
In the evening, he decides to pay his bill and head out. When I reach his villa, there are housekeepers waiting around for a tip. Mr. VIP pays his bill, eyeballs each housekeeper, and then tosses a bunch of cash on the bed, calling it only for "Dimitry". So we head to the pier and off he goes.
51. Meat Me Halfway
When I waited tables, this older lady and her younger guy pal came into my restaurant. She ordered steak and a baked potato. I served it up and asked if she needed anything else. Her answer blew me away. She said, "Yeah, chop that steak into bite-size chunks. And smear that butter and sour cream on the potato, season it, then go ahead and dice it as well".
Just as it dawned on me she wasn't joking, my smile dropped and my jaw did the "slow sag of disbelief" thing. Her friend noticed I was about to pop off with some not-so-nice words, so he jumped in and said he'd handle it. I still shake my head over that woman's nerve to ask that.
52. Embrace The Suck
One of my army pals was a wealthy kid. He joined the military mostly for his resume, probably for his future political career. I get it, since I also joined for resume credit. But, he really didn't care about the job. He'd pay others a grand just so he could skip his duty.
Every couple of months, he'd have a new high-end European car. Once, he ran out of gas and just left his car on base, got a rental, then bought a new car off base. Our whole team couldn't stand him. So much that my team leader posted him far away in an Afghan cave.
We did this to protect ourselves and stop him from messing up. Last time I heard, he was posted at the Pentagon. When I worked there, I saw him, and he seemed more like a secretary than anything. Yet, he always acted like he was a hotshot. People would simply say, "Hey, guy", since nobody bothered to remember his name.
As I mentioned, it's all about the resume for him. Money doesn't matter; power does. He's an egoistical jerk who I bet will be a successful politician soon, given how similar he is to most of them.
53. Where There’s A Will…
My grandpa passed away, leaving behind $20 million. He lived in an old-school one-bedroom condo, drove a beat-up Honda, and his wardrobe hadn't been updated in a decade - all Walmart specials. When we read his will, I was shocked to see various distant relatives show up, no doubt hoping to grab a share.
First off, he didn't forget any of them in his will. He took a jab at every single one. After he'd had his fun, he filled the next ten pages with the list of charities and foundations he was leaving all his fortune to. One tidbit that surprised everyone? He secretly owned 160 acres of lush forest land in Vermont, which no one but him knew about. This he donated to a land trust to be converted into hiking trails.
54. Hold The Phone
I used to hawk cell phones at a store and had to sell a certain amount of insurance plans each day. One time, this super loaded lady bought four of the latest iPhones for her and her fam. I pitched her our insurance plans. Her response gave me the creeps.
She basically said since she's stacked, she wouldn't bother with insurance and would just buy new phones if anything went wrong. This was in 2018, so these flashy iPhones cost her a grand each. I pushed the insurance aspect a bit, because without it, a $4,000 sale would dent my daily stats. I mean, four grand is a serious chunk of change.
So, I sold it as, "What happens if the phone gets wrecked or the screen cracks"? That's when things got real messed up. She got so ticked off that to prove her point, she bought four extra phones as backup. Then she started ripping into my sales skills and rubbing it in my face about being poor and studying in college.
I guess she heard me complaining about it to a friend at work. I wasn't rattled at first. But then, after I'd set up one of her new phones, she took things too far. She strolled to a non-carpeted part of the store and deliberately dropped it, smashing the screen.
She came back to me and asked me to set up a fresh phone. She totally undermined me, but I was stuck. I couldn't say no to a customer who just shelled out $8,000 in our store.
55. Dude Needs To Off-Gas
A friend of mine used to room with a wealthy guy. This dude had a thing about wearing fresh socks daily but the catch is, instead of washing the used ones, he just tossed them. Thought it'd make him super clean, but it ended up going south. Over time all the chemicals from those new socks gave him a nasty foot rash.
Sources: Reddit
